To think my friend is trying to make me feel bad?

You sound like a decent person OP who wants to help others.

But frankly your 'friend' sounds like she only wants you around if she can make you feel bad so she can feel better about herself.

Basically when you were struggling she probably felt a sense of satisfaction that she was not in your position...now that she is struggling too she is trying to bring you down so she can feel superior again.

I would dump her and focus on making new friendships with people who bring positivity to your life.

This is a person unhappy with their life who finds pleasure in trying to make you as miserable as them. Personally I would end this ‘friendship’ but I would not just ghost them, I’d call them on their behaviour so that they would stop it or choose to drop me - that’s just my style.
When they brought up the estrangement again, I would say something like ‘I’ve asked you to drop the matter so why do you continue to ask me?’ Accusations of sensitive - ‘yes perhaps, and you know this so why do you keep asking. Is your intention to upset me?’. “mothers love is unconditional” - ‘again, you keep referencing matters you know will hurt me - why?’.
If there is anything that would result in a similar response for her, I would use it ‘How would you feel if we spent this call discussing your x instead if you wish to raise hurtful topics?’ A final one if she was persistent would be ‘you seem to be using this call just to bring up matters I’ve asked you not to so I’m going to end it now as I’ve made my position clear’ then hang up. Then I would not contact her again. If she contacts me, OK, I’ll talk but when she raises this again I would go through the same routine. She will get the message that access to me relies on accepting my boundaries. If she is as sensitive as you say, she will probably not contact you after you call her out on her behaviour.

I'm so sorry, but this woman is not your friend. She's part of your toxic past and what's more, she's happiest when you're upset. She doesn't sound like a nice person at all - she sounds greedy and entitled, tbh.

Given she lives so far away then I'd either block her or I'd get another phone number altogether so that she can't get hold of you. I'd ask your husband to monitor any messages that arrive through the post because she will certainly try to drag you back into her life, especially as she's lost her other friends (wonder why?) and you give her money.

I have some years of my life that I am really trying to put behind me and I get really anxious/(pissed off) when anyone mentions this.

I shut it down and say that's a time in my life that I've moved on from. I really can't talk about that any more.

Eventually the message gets through but I get you must be really disappointed in your friend who continues to bring up triggering subjects.

You might decide that you need to distance yourself from the friendship.

X

But this has happened so many times you have no excuse now for not preparing a good response.

Just practise a couple and deliver them - clearly and firmly.

I’ve asked you not to keep bringing that up. I expect you to respect that.

If you can’t respect that, I think it would be best if we stopped talking. (end call.)

Shes walking all over you and you’re letting her. Call her out on it and protect yourself.

A friend would not.

I’m guessing your family are very toxic or you wouldn’t be no contact. It seems you have a toxic friendship too. When we grow up around toxic people we attract them as adults because it’s what we’re used to, until (if we’re lucky) we start having a sort of awakening and making changes.

I’d say leave her in the past and move forward. She’s dragging you back.

Try to get some boundaries in place OP.

I have a similar dynamic with a friend nowadays. She’s going through a rough patch. I’ve tried to help. I’m also going through a terrible patch, but she doesn’t even know about any of it. The reason she doesn’t know is she will call and tell me every negative thing in her life for two hours then go. Or I’ll text something nice and get a list of awful things going on in her life. In reality she has nice things happening too but I’m not told about them.

the part that resonates with me is I’m estranged. My friend also knows this and I get the nasty comments about it. Even when i say I don’t want to talk about it or its the same. It’s like my family estrangement has to be a topic of conversation always.

we haven’t spoken on the phone now for 6 months which is sad but at least I don’t have salt rubbed in my wounds.

This person is not a positive force in your life. You have shared history which makes it hard to cut her out but she seems so toxic. She is needling you, it’s nasty and a problem with her. We all have things in our past that we don’t want to discuss/revisit. Speaking from experience of a similar person, I would avoid. Hope you’re ok.

OP this is no friend!!! Fade fade fade her out of your life. She sounds horrible!

She doesn't sound much of a friend, Op. Perhaps she was in the past but not now?

She's deliberately talking about a subject which is deeply painful to you and which you don't want to discuss with her. This isn't you being 'sensitive', it's self-preservation and she is being very insensitive. I'd be asking myself what is she getting out of doing this when she knows it upsets you so much?

I had a very similar situation with a cousin of mine. I rarely heard from her but whenever I did she would bring up a very painful situation from my childhood which had affected me but not her. Like you, I expressed my boundaries to her and she would ignore them. I believe she was getting some sort of warped pleasure out of stirring things up. The last time she did it, I very calmly told her I wasn't going to discuss the subject, she tried to change my mind, I told her 'no' a second time and ended the call. Then I blocked her. Some people don't deserve our friendship. Only you can decide whether this friendship is worth having any longer.

Stop answering her calls and replying to her texts. You're under no obligation to continue a relationship with someone who is unkind to you and upsets you. Friendships should bring joy into your life - if they're not, then they are not a good friend.

Voted YABU for staying friends.
When your friends drag you down, walk away.

Nah, get rid OP. As a previous poster says the friendship has run its course.
I've had this dynamic and after losing my shit didn't change anything, I phased them out. With hindsight they liked me being in a negative space and when I did something about it and changed things for the better the jabs started and they were nothing as bad as what she's saying to you. It's an appalling way to treat a friend of 20 years.

She's bringing up your past issues to feel better about her own problems. And she doesn't respect your boundaries when you tell her that you don't want to dig the past back up, which suggests that she doesn't give a shit about you or your feelings. The forgotten birthday further reenforces my conviction that she's not your friend. I'd be done with her. But if you're not ready for that, at least stop giving her money, supprt or offers of help. Just be cordial and polite, and keep it at that.

She's just horrible and she's not your friend.

There's a difference between a request, ("Please don't bring up X", where she's got the power, either to respect or ignore) and a boundary ("I don't want you to bring up X ever again, and if you do, I'll hang up"/ "I asked you not to bring up X, you have, so I'm hanging up now" where you have the power.
You need to have boundaries and protect them.
This woman is not your friend. She may have problems but her putting you down to make herself feel better doesn't help either of you.
Unfortunately there are "friends" who are happier when you're down and she's one of them.
Long-term, you're doing her a favour by enforcing boundaries, because she'll have to find better ways of making herself feel good.
I'm glad you're in a better place now and hope things continue to get better and that you make some really good friends, who enhance your life and who make you feel buoyed up after seeing them. You deserve better than someone who causes you repeated pain.💐

in the moment it’s like I’m stunned and frozen

So have some stock answers written down and refer to them if she phones and starts saying this stuff. Maybe you could write/e-mail and lay out your concerns if that is easier than the immediacy of a voice on the phone. Give her some time to consider and change her ways. Mainly, I'd say she isn't much of a friend and you should distance yourself from her. You are not at her beck and call.